Why the Impossible Connects the Most

A Tribute to David Cummings

I was lying in bed last night and checked my email one last time. I saw the daily email from my friend David Cummings and was shocked when I opened it.

“Today marks blog post number 3,000! I’ve been blogging daily for over eight years, and it’s time to mark the end,” wrote David.

David Cummings is done with his daily blog. He won’t stop sharing his wisdom, startup lessons, and recaps on how companies are valued. He’s just not going to do it every day. He said, “I’m only going to blog when I have a topic or idea I really want to share.”

I know exactly how he feels. I’ve had friends come to me and say, “I don’t know how you do it. Two blogs a week would wear me out.”

You know what? It will wear anyone out, including me. Blogging twice a week makes my blog one of the highest priorities in my life. Every day I wake up and think, “I have to write a blog today. What on earth am I going to write about?”

There are three types of blogging weeks for me.

1. The Easy Post

I have a meeting with an entrepreneur, and a blog pops out from our conversation. I have lots of conversations, but every once in a while, a pearl, an insight, or bit of unique and usable wisdom is in the conversation. Sometimes it is just an interesting conversation to relate.

These stories flow easily. I have high confidence it will be valuable to you, my entrepreneur audience, because it was valuable to the entrepreneur I was talking to and to me. These stories are relevant because the blog addresses an issue an entrepreneur was having today. And his struggle reminded me of my struggle.

2. The Hard Post

As an angel investor and student of entrepreneurs and startups, I’m always trying to figure out patterns and behaviors. What works? What doesn’t work? Why did this guy win big? Why didn’t this guy last a year? Why do so many entrepreneurs get stuck in the rut of a $1mm-a-year business? Why is cash flow so easy to understand and so difficult to practice? What is right in front of me that has the answers to these questions?

Ideas pop into my head at the weirdest times. I could be reading the Bible. I might be brushing my teeth or talking to a friend about nothing related to entrepreneurs and bang, I get an idea. I have even had my eyes pop open in the middle of the night from a restless sleep. Every time this happens, I grab my phone, open Evernote, and write down the idea and some thoughts around it.

The hard part is going back to these ideas and creating a blog from them. The best blogs are like the “easy” ones above. I’m excited about an idea and have just the right story to tell which relates it to you. Without this, it is just an idea. It is like a good quote. You read it and think it’s really insightful but forget it in the next two seconds. A good idea communicated in a great story is the key to retention. Stories connect with our experience. This connection creates the retention and application.

3. The Impossible Post

This is when I start the week with no ideas. Worse yet, I am not motivated. I start the week in a funk or depression. Then the negative self-talk kicks in.

  • “I have nothing to offer.”
  • “Does any of this writing make a difference to anyone.”
  • “Maybe I should just stop writing. I’ve done enough.”

I could continue to share the negative conversation in my head, but you get it.

Then I bump into someone who says, “I read your blogs, and they really make a difference in my life. In fact, I pass them on to my friends who thank me for sending the blog posts to them.”

When I hear this, I don’t know what to say. I was so sure the blogs were worthless, I am stunned at the value this person sees in them. I leave the conversation feeling encouraged but stuck. Now what? I don’t want to do it anymore but believe I have to do it.

Here is a description of a day when I am really stuck. It is the day the blog must be written, and I still have nothing. I am a blank slate.

I call my editor, Gregg Hinthorn, and say, “This sucks. I got nothin!”

He proceeds to talk me off the ledge.

“Just tell your readers what you are going through right now. They go through these same emotions. By writing about what is happening today, you’ll be helping you and them,” Gregg says.

I follow his advice and write the blog post.

Without a doubt, these blog posts result in the greatest connection. No insights, no wisdom, just sharing.

David Is Superman

Writing and publishing every day makes David Superman in my eyes. Eight years of daily blog posts. Think about it. David is a very private man. He’s a great success and contributor to our startup community, but he is quiet. But he is a man, nonetheless, who has experienced daily the challenge of the easy, the hard, and the impossible of blogging.

Thank you, David

On behalf of the entire community, we owe you a debt of gratitude, David. I have many of your blog posts saved in my “blogging ideas” folder in Evernote. I just need a good story to make them come to life for my readers. And, for me, that makes them “hard.”

I look forward to reading more of your posts for many years to come. You’ve shared your wisdom and experience. For that, you’ve blessed all of us. Thank you.

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